An unexpected lunch invitation

as far as attire, if during the work week I'd go maybe suit with no tie, if on the weekend smart casual is fine. it also depends on the venue, if he wants to meet you at a bar, dress more casually, say jeans with a sportcoat.

here's how I approached all of my informational interviews

1. get them talking about them. questions like how did you get your start, what was the most interesting deal you ever worked on, why this career vs others, how did you end up at your prior ship, things like that. you want them to tell their story. the goal of this is not to impress I don't think but to learn.

2. offer up bits of yourself when appropriate. oh, I play squash too! oh, I went to catholic school too, and so on.

3. ask him what he'd do if he were in your shoes and his goal was ____ (whatever your goal is), assuming he hasn't already told you.

4. ask him for help in one of 2 ways, both of which are fine. is there anyone in ___ industry that you think I should meet? or the less abrasive if I find someone who I'd like to meet and there's a chance you know them, would you mind giving an introduction?

I personally prefer the latter because it gives you something to follow up with them about, and also because they're not likely thinking of people they know off the top of your head. you should connect with him on linkedin and troll his connections. a college kid in my area did this, noticed I went to school with someone in PE in our same city, and he followed up by asking me if I knew him and would be willing to connect them. it turned out we're very good friends, and he has since met with the kid as well.

here's the deal: most people who will take the time to meet with you have some similar past of struggling or hustling to find work, they respect the hustle. but theres also a lot of social klutzes out there who we wouldn't want to be associated with. if he gave you the meeting, he's willing to help. the number one thing he's probably trying to ascertain is if you are not so awkward or lazy that he can't stick his neck out for you. that's all I did, asking myself: "would I be comfortable introducing this kid around?"

just relax, be yourself, be intentional about the discussion, but above all else, get him talking about himself, it's a much better way to build rapport than to recite some stupid elevator speech about how much you love finance.